2-(5-(5-Amidinothiophen-2-yl)furan-2-yl)-1H-benzimidazole-5(6)-amidine

ID: ALA4159258

PubChem CID: 145958597

Max Phase: Preclinical

Molecular Formula: C17H14N6OS

Molecular Weight: 350.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2nc(-c3ccc(-c4ccc(C(=N)N)s4)o3)[nH]c2c1

Standard InChI:  InChI=1S/C17H14N6OS/c18-15(19)8-1-2-9-10(7-8)23-17(22-9)12-4-3-11(24-12)13-5-6-14(25-13)16(20)21/h1-7H,(H3,18,19)(H3,20,21)(H,22,23)

Standard InChI Key:  UUWSLLFRNHISGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   16.3011  -16.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3000  -16.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0080  -17.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0062  -15.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7149  -16.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7151  -16.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4981  -17.1369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9818  -16.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4977  -15.8050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7973  -16.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2779  -17.1316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0550  -16.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0547  -16.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2774  -15.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7161  -17.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7164  -18.1728    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4937  -18.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9738  -17.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4932  -17.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7465  -19.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1999  -19.8096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5459  -19.3718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5920  -17.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8846  -16.8816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5913  -18.1079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 10  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  2  0
 12 15  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
  2 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4159258

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 350.41

Molecular Weight (Monoisotopic): 350.0950

AlogP: 3.12

#Rotatable Bonds: 4

Polar Surface Area: 141.56

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.26

CX Basic pKa: 11.37

CX LogP: -0.09

CX LogD: -1.81

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.28

Np Likeness Score: -0.72

References

1. Farahat AA, Ismail MA, Kumar A, Wenzler T, Brun R, Paul A, Wilson WD, Boykin DW..  (2018)  Indole and Benzimidazole Bichalcophenes: Synthesis, DNA Binding and Antiparasitic Activity.,  143  [PMID:29126729] [10.1016/j.ejmech.2017.10.056]

Source

Source(1):

• Scientific Literature